Year: 1986

It doesn't get any crazier than this. It was 1986, rappers were in a music video with Aerosmith, rocking sneakers that they eventually got paid $1.6 million to wear. Moments like this are why a hip-hop trio could call themselves the kings of rock. In one fell swoop, they'd created a trend and asserted themselves as the most important act on the block, the boardroom, and the pop charts. Don't even think about putting laces in those shelltoes, either.